Soya amidopropyldimethylamine oxide

ABSTRACT

A COMPOSITION AND METHOD FOR STABILIZING THE FORM OF ANIONIC SURFACE ACTIVE GENT BY ADMIXING THE ANIONIC SURFACE ACTIVE AGENT WITH AN AMIDO-AMINE OXIDE HAVING THE GENERAL FORMULA:   R-CO-NH-(CH2)3-N(=O)(-CH3)2   WHEREIN RCO IS DERIVED FROM THE FATTY ACIDS IN SOYA BEAN OIL.

United States Patent 3,740,351 SOYA AMIDOPROPYLDIMETHYLAMINE OXIDE Saul Kaplan, Teaneck, Kenneth W. Protlo, Westfield, and

Edward G. Shay, Belle Mead, N.J., assignors to Millmaster Onyx Corporation, New York, N.Y.

N0 Drawing. Original application Aug. 12, 1969, Ser. No. 849,516, now abandoned. Divided and this application Mar. 22, 1971, Ser. No. 127,043

Int. Cl. Clld 7/32 US. Cl. 252547 2 Claims ABSTRACT OF THE DISCLGSURE A composition and method for stabilizing the foam of anionic surface active agents by admixing the anionic surface active agent with an arnido-amine oxide having the general formula:

/CH3 R C ONHCHZCHQCI'IZN wherein RC0 is derived from the fatty acids in soya bean oil.

This is a division of co-pending application Ser. No. 849,516, filed Aug. 12, 1969, now abandoned.

This invention relates to a low-cost foam-stabilizing agent for anionic detergents and particularly for detergents based on sulfated fatty alcohols. The said agent is an amidoamine oxide having the general formula:

is derived from the fatty acids in soya bean oil.

Amine oxides are well known to the art and are used for various purposes in detergent compositions. They are usually prepared by alkylating a secondary amine followed by oxidation with ozone or more frequently with a peroxide, such as hydrogen peroxide. The alkylating agents, of moderate to long chain length, are generally of the alkyl halide variety, and are relatively costly to prepare.

The present invention employs instead a carboxylic acid of suitable chain length, and of low cost. The fatty acids contained in soya bean oil are especially desirable for this purpose, and the naturally occurring glycerides may be used without intermediate steps such as saponification, hydrolysis, distillation and the like, although the free fatty acids may be used instead, or their other esters such as the methyl esters, if so desired. The following Example 1 describes the preparation of the amidoamine from an ester. The preparation from free fatty acids differs in that water formed in the course of the condensation must be removed, azeotropically or otherwise. Example 2 describes a typical and effective method of preparing a solution of the amine oxide from the soya amido-amine.

The examples following are merely illustrative and are not intended to limit the invention, except as claimed.

Example 1 A two-liter round-bottom flask fitted with an agitator, a thermometer and a reflux condenser was charged with the following mixture, and heated to about 160170 C.,

Patented June 19,, 1973 at atmospheric pressure, under a blanket of nitrogen suflicient to prevent the access of air, for a period of about six hours, or until the reaction was essentially complete.

Charge:

Soya bean oil 583 g. (Vs mol). Dimethylaminopropylamine 204 g. (1.96 mol).

612 grams of the product of Example 1 were charged into an agitated round-bottom flask with a thermometer and a reflux condenser, along with 141 grams of 35% hydrogen peroxide solution, 1,100 grams of water, and about 0.7 gram of a chelating agent such as a salt of ethylenediamine tetraacetic acid.

The mixture was agitated and heated gradually to 7080 C. for a period of about two hours, or until the reaction was essentially complete. During the course of the reaction, the charge thickened and eventually gelled and was no longer stirrable. Thereafter, it thinned out and became a readily stirrable' clear, light-colored liquid of a single phase. The heating was continued until titration of samples showed essential completion. These indicated an amide-amine oxide content of 34.0%, unreacted amido-amine of 0.87%, and 0.22% of hydrogen peroxide.

Example 3 In a manner similar to the procedures of Examples 1 and 2, the homologous amidopropyldimethylamine oxides were prepared from tallow and from coconut oil. These were tested along with the product of Example 2 and are tabulated in the following Example 4.

Example 4 The product of Example 2 was added to coco fatty alcohol sulfate salt of commerce, and the amount and stability of foam was determined by the use of the Ross- Miles procedure as described in the A.S.T.M. Standards of 1958, pp. 878 et seq., A.S.T.M. designation D-1173-53 (Foaming Properties of Surface-Active Agents). In conjunction with this, the tallowand cocoyl-amidopropyl dimethylamine oxides of Example 3, and also a commercial grade of stearyl dimethylamine oxide, were used.

The surface-active agents employed were Maprofix TLS-SOO (Millmaster Onyx Corp.), a triethanolamine lauryl sulfate, and Maprofix WAC (Millniaster Onyx Corp.), a sodium lauryl sulfate. Each of these was diluted to contain 20% by weight of active alkyl sulfate material.

Each amine oxide added, in the following tables, is the actual weight percent of active amine oxide material added to the surfactant.

Jersey City tap water, as used in the tables, has a hardness of about 30 parts per million as CaCO Synthetic hard water employed in Table 3 contained 300 p.p.m. of hardness.

Foam heights in the tables, both for the initial readings and for those five minutes later, are in millimeters. AAO represents amide-amine oxide; DMAO represents dimethylamine oxide.

TABLE 1.-MAPROFIX TLS 500 Ross-Miles foam test in tap water at; 40 0., amine oxide type Soya AAO Tallow AAO Gocoyl AAO Stearyl DMAO Wt. percent amine oxide Initial 5 min. Initial 5 min. Initial 6 min. Initial 6 min.

TABLE 2.MAPROFIX WAC Soya .AAO Tallow AAO Cocoyl AAO Stearyl DMAO Wt. percent amine oxide Initial 6 min. Initial 6 min. Initial 6 min. Initial 6 min; 3:s:::::::::::::::::::::::::::: 3%? 538 ii? iii 22% 393 3%? 398 TABLE 3.MAPROFIX TLS-600 Ross-Miles test in 300 p.p.m. hard water at 40 C.

Soya AAO Tallow AAO Cocoyl AAO Stearyl DMAO Wt. percent amine oxide Initial 6min. Initial 6min. Initial 6min. Initial 61min.

The data tabulated above demonstrates the effective- 0 ness of the low cost soya amidopropyl-dimethylamine ll oxide in relation to that of the higher cost long chain H H alkyl tertiary amine oxides. 0 CH3 Although only triethanolamine lauryl sulfate and sodiwherein um lauryl sulfate have been disclosed above as used in the tests, it is not to be inferred therefrom that only these are included. They have been used only for illustrative purposes. In fact, any of the anionic surface active agents, such as disclosed in Surface Active Agents and Detergents, Schwartz, Perry and Berch, Interscience Publishers, Inc., New York, N.Y., 1958 (vol. II), pp. 25-102, may be used, such, for example, as the various alkyl sulfates and ether sulfates, both straight chain and branched chain, including the oxo-derived types; and the sulfonates such as the alpha-olefin sulfonates, alkyl aryl sulfonates and the like, which are used for detergent purposes.

The invention claimed is:

1. A foam stabilizing composition consisting essentially of an ionic surface active agent and a foam stabilizing agent, said foam stabilizing agent being present in sufficient amount to increase the foam stability of the composition, such foam stabilizing agent being a substantially unsaturated amine oxide having the structure:

References Cited UNITED STATES PATENTS 8/1939 Guenther et a1. 252--547 7/1963 Dohr et a1. 252-547 7/1968 Lamberti 260404.5

OTHER REFERENCES Baileys Industrial Oil & Fat Products (3rd), Interscience Pub. (1964), pp. 224-226.

WILLIAM E. SCHULZ, Primary Examiner U.S. Cl. X.R. 

